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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 4
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Original Articles

Convenient Preparation of Optically Pure 3‐Aryloxy‐pyrrolidines

, , , , , , , , & show all
Pages 517-524 | Received 21 Aug 2007, Published online: 27 Feb 2008
 

Abstract

Chiral 3‐methanesulfonyl‐1‐Boc‐pyrrolidine and piperidine were reacted with sodium phenolates, resulting in a mixture of displacement and elimination products. Following carbamate deprotection and pH adjustment, the 3‐pyrroline and tetrahydropyridine by‐products resulting from elimination were easily removed through aqueous partitioning and/or concentration. Although the pyrrolidines were formed with a high degree of optical purity, slight racemization was observed for the piperidine case because elevated temperatures were required to effect displacement.

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